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A.

Title Of Experiment
: Carboxylic Acid
B. Date Of Experiment
: Thursday, 10th March 2016 , 01.00 04.00 PM
C. Purpose Of Experiment :
1. To prepare the simplest carboxylic acid in laboratory,
example formic acid
2. To understand the principal of carboxylic acid such as
decarboxylation, oxidation, and esterification.
D. Basic Theory
A carboxylic acid is an organic compound containing the carboxyl group
,-CO2H. the carboxyl group contains a carbonyl group and hydroxyl group. The
interactions of these two groups lead to a chemical reactivity that is unique to
carboxylic acids.
(Fessenden and Fessenden, 2008: 597)
The characteristic functional group of the carboxylic acids is the carboxyl
group,

(Cason, 1956: 120-121)


The simplest carboxylic acid is formic acid, HCOOH. Those compound can
make from decarboxylation reaction from oxalic acid. The reaction is

+CO2
In the laboratory, formic acid can be obtained by heating oxalic acid in
glycerol and extraction by steam distillation. Glycerol acts as a catalyst, as the
reaction proceeds through a glyceryl oxalate intermediary. If the reaction mixture is
heated to higher temperatures, allyl alcohol results. The net reaction is thus:
C2O4H2 CO2H2 + CO2
Another illustrative method involves the reaction between lead formate and
hydrogen sulfide, driven by the formation of lead sulfide
Pb(HCOO)2 + H2S 2HCOOH + PbS
(Sutcliffe, 1930: 167)
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The whole CO2H group is removed from the molecule, leaving the
carbonyl group at the

- position chenie, all that

stuff 1 mentioned a

minute ago. This happens either when theres a ketone at the -position.
Formic acid easy to oxidation produce CO2 if formic acid react with
KMnO4. The reaction is:
HCOOH+ 2 MnO4- 3 CO2+ 2 MnO2 (brown)+ 2 OH-+2 H2O
Some of the carboxylic acid
Numbe
r of
Carbon
s
1
2
3

Structure

Trivial Name

Occurrence and
Derivation Name

HCO2H
CH3CO2H
CH3CH2CO2H

formic
acetic
propionic

4
5

CH3(CH2)2CO2H
CH3(CH2)3CO2H

butyric
Valeric

6
7

CH3(CH2)4CO2H
CH3(CH2)5CO2H

Caproic
Enanthic

8
9

CH3(CH2)6CO2H
CH3(CH2)7CO2H

Caprylic
Pelargonic

10

CH3(CH2)8CO2H

capric

Ants (L. Formica)


Vinegar (L. Acetum)
Milk, butter, and
cheese (Gr. Protos, first
; pion, fat)
Butter (L. Butyrum)
Valerian root (L.
Valere, to be strong )
Goat (L.caper)
(Gr. Oenanthe, vine
blossom)
Goat
Its ester is found in
Pelargonium reseum, a
geranium.
goat

Physical properties of carboxylic acids


1. Boiling points
The boiling points of alcohols are higher than those of
alkanes of similar size because the alcohols can form hydrogen
bonds with each other as well as van der Waals dispersion
forces and dipole-dipole interactions. The boiling points of
carboxylic acids of similar size are still higher.
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For example:
propan-1-ol

CH3CH2CH2O

97.2

ethanoic

H
CH3COOH

C
118

acid

These are
chosen

for

comparison because they have identical relative molecular masses and


almost the same number of electrons (which affects van der Waals
dispersion forces).The higher boiling points of the carboxylic acids are
still caused by hydrogen bonding, but operating in a different way. In a
pure carboxylic acid, hydrogen bonding can occur between two
molecules of acid to produce a dimer.

This immediately doubles the size of the molecule and so


increases the van der Waals dispersion forces between one of
these dimers and its neighbours - resulting in a high boiling
point.
2. Solubility in water
In the presence of water, the carboxylic acids don't
dimerise. Instead, hydrogen bonds are formed between water
molecules and individual molecules of acid.
The carboxylic acids with up to four carbon atoms will
mix with water in any proportion. When you mix the two
together, the energy released when the new hydrogen bonds
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form is much the same as is needed to break the hydrogen


bonds in the pure liquids.
The solubility of the bigger acids decreases very rapidly
with size. This is because the longer hydrocarbon "tails" of the
molecules get between water molecules and break hydrogen
bonds. In this case, these broken hydrogen bonds are only
replaced by much weaker van der Waals dispersion forces.
Characteristic of carboxylic acid:
1. Esterification reaction
Carboxylic acid esther is the compound that contain group
function
COOR with R can form alkyl. Ester can be formed because the
appearance of direct reaction between carboxylic acid and
alcohol. The reaction commonly:
RCOOH + ROH HCOONa + H2O
The carboxylic acid and alcohol combination used to
prepare an ester are reflected by the name of the ester, e.g.
ethyl acetate (or ethyl ethanoate), CH3CO2CH2CH3 can be made
from CH3CO2H, acetic acid (or ethanoic acid) and HOCH 2CH3
(ethanol). This general "disconnection" is shown below:

The Fischer esterification proceeds via a carbocation mechanism. In


this mechanism, an alcohol is added to a carboxylic acid by the following
steps:
1. The carboxyl carbon of the carboxylic acid is protonated.

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2. An alcohol molecule adds to the carbocation produced in Step


1

3. A proton is lost from the oxonium ion generated in Step 2.

4. A proton is picked up from solution by a hydroxyl group.

5. A pair of unshared electrons from the remaining hydroxyl


group helps the water molecule leave.

6. The oxonium ion loses a proton to generate the ester.

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7. Esters can also be prepared in a nonreversible reaction of an


acid with an alkoxide ion

2. Oxidation reaction
Because it is already in a high oxidation state, further
oxidation removes the carboxyl carbon as carbon dioxide.
Depending on the reaction conditions, the oxidation state of
the remaining organic structure may be higher, lower or
unchanged. The following reactions are all examples of
decarboxylation (loss of CO2). In the first, bromine replaces the
carboxyl group, so both the carboxyl carbon atom and the
remaining organic moiety are oxidized. Silver salts have also
been used to initiate this transformation, which is known as
the Hunsdiecker reaction. The second reaction is an interesting
bis-decarboxylation, in which the atoms of the organic residue
retain their original oxidation states. Lead tetraacetate will also
oxidize mono-carboxylic acids in a manner similar to reaction
#1.

Finally,

the

third

example

illustrates

the

general

decarboxylation of -keto acids, which leaves the organic


residue in a reduced state (note that the CO2 carbon has
increased its oxidation state.).
3. Decarboxilation reaction
Decarboxylation is the loss of the acid functional group as
carbon dioxide from a carboxylic acid. The reaction product is
usually

halo

compound

or

an

aliphatic

or

aromatic

hydrocarbon.

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Mechanism of Decarboxylation:
Step 1:
Start at the prot pronation
of the carbonyl, break the
O-H bond and form the p
bond, break the C-C and
make the C=C. Note the
concerted nature of this
reaction and the cyclic
transition state
Step 2:
Tautomerization of the enol of
the carboxylic acid leads to the
acid product (not shown here).

Esters are produced when carboxylic acids are heated with alcohols in
the presence of an acid catalyst. The catalyst is usually concentrated sulphuric
acid. Dry hydrogen chloride gas is used in some cases, but these tend to
involve aromatic esters (ones containing a benzene ring). If you are a UK A
level student you won't have to worry about these.
The esterification reaction is both slow and reversible. The equation for
the reaction between an acid RCOOH and an alcohol R'OH (where R and R'
can be the same or different) is:

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So, for example, if you were making ethyl ethanoate from ethanoic acid
and ethanol, the equation would be:

Carboxylic acids and other carbonyl-containing compounds with an additional


carboxyl group located on the -carbon are subject to decarboxylation
reactions. In these cases the carboxyl group is lost as carbon dioxide and this
reaction can occur because the remaining carbonyl can readily accept the
electron pair left in the reaction. Again, this reaction occurs because the charge
formed by decarboxylation is stabilized by resonance through the carbonyl
system as shown below:

Reaction of an alcohol with an acid yields the type of compound known


as an ester, so this process is known as esterification. The reaction is a
reversible one which is catalyzed by acid, as illustrated in equation:

Since this area is an equilibrium, it follows that the same poin of


equilibrium is reached weather we start with an acid and alcohol, or an ester
and water. If we wished to hydrolyze an ester, we could drive the equilibrium
to the left by use of a very large excess of water because water is such a cheap
reagent. If we are interested in making an ester, however, we must adobt some
means of driving the reaction to the right. If either the acid or alcohol is cheap
we may conveniently use an excess of that reagent, and this usually done if
methyl as ethyl alcohol is being used. Although devices may be used to remove
the water from the reaction and thus drive is forward, this process for making

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ester is commonly used when one of the reactions is sufficiently cheap to be


used in excess.
Attention should be directed to the fact that an ester is an entirely
covalently bonded compound, and therefore has entirely different properties
from a salt. This fact is emphasized because esterification bears

formal

resemblance to salt formation. Since in this both case the acid react with a
hydroxyl, containing compound and water is one of the products. The entirely
covalent nature of the bonds in an ester, however, give it the usual properties of
organic compound, relatively low boiling point, in solubility in water,
solubility in organic solvents. These properties are in marked contrast to those
of n alkali metal salt of an acid, with contains one electrovalence. (Cason,
1956: 120-121)
Ethyl ethanoate C4H8O2 is an organic compound is a
liquid, colorless and 770C boiling point, refractive index of
1.372, fragrant smell (aroma), volatile. In everyday life ethyl
acetate serves as the smell of food (essence) and solvent
organic compounds. Ethyl ethanoate / ethyl acetate prepared
by esterification reaction of acetic acid with an alcohol
compound in acid and heated atmosphere
Compounds which can be considered to be derived from
a carboxylic acid with hydrogen from group function replacing
hydroxyl with a hydrocarbon group called Esther. Presumably
most common ester is ethyl acetate CH 3CO2CH2CH3, a solvent
commonly used in many solvent. Ethyl acetate and other
esters with carbon ten or less a volatile liquid with bad smell
like fruits
A carboxylic acid ester is a compound contain -CO2R
group with R can be alkyl or aryl-shaped. An ester may be
formed by direct reaction between a carboxylic acid and an
alcohol, a reaction called esterification reaction.

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E. Tools And Materials


1.
a.
b.
c.
d.
e.
f.
2.
a.
b.
c.
d.
e.
f.
g.
h.
i.
j.

Tools
Distillation flask
1 piece
Liebig Condenser
1 piece
Test tube
3 pieces
Erlenmeyer flask
1 piece
Bunner
1 piece
Gradauated cylinder 1 piece
Materials
Oxalic acid
2.5 mL
Glycerol
5 grams
Glacial acetic acid
2 mL
Ethanol 96 %
4 mL
Ca(OH)2 Solution
CH3COONa 10 % solution 5mL
KMnO4 1 N solution 3 mL
FeCl3 5 % solution
3 mL
K4Fe(CN)6 1 M solution
Concentrated sulfuric acid 12 mL

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F. Procedural
1) Preparation of formic acids and reactions happen in formic acid

2) Acetic acid Reactions

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3)Glacial
Esterification
aceticReaction
acid 2 mLEthanol 96% 28mL
mL of Concentrated sulfuric acid

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Poured into test tube


and
12Heated by steam bath
GROUP
5 -closed
PKU14it
Cooled it
Result + odor

Ethanol 96% 2 mL

H2SO4 4 mL

Poured into test tube


Heated by steam bath and closed it
Cooled it
Result + odor

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G. Observation Result
N
o
1

Experiment Procedural
Preparation of Formic Acids and reactions happen in
formic acid

Observation Result
Before :
H2C2O4 (s) = White
Crystal
Glycerol = Colorless
KMnO4 (aq) = Purple
CH3COOH(aq) =
Colorless
Lime water = colorless

Hypothesis/ Reaction
- H2C2O4 (aq) +

14

(CH2)2CH(OH)3
HCOOH(aq) + CO2 (g)
- CO2 (g) + CO(OH)2(aq)
CaCO3(s) + H2O(l)
- 2 HCOOH(aq) + 2
KMnO4 3CO2 (g) +

MnO2 (s) + 2 KOH +2


After :
H2O (l)
H2C2O4 (s) + Glycerol =
- CH3COOH(l) + KMnO4
colorless
After heated, H2C2O4 (s) + - CH3COOH(l) +
KMnO4(aq)
Glycerol = Soft yellow
Formed gas CO2 , after it
Ran at lime water =
Lime water keep color
less
Solution in destillation
flask + 2,5 gr H2C2O4 (s) =
Soft yellow
The result of destillaton
process is Formiac acid
= color less

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Conclusion

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Formic acid can


produce
from
decarboxylation
of
H2C2O4 with use
catalist glycerol and
the other produck is
carbon dioxide.
The
function
of
KMnO4 is oxidator

Acetic Acid Reactions

Volume Formiac acid is


1 ml
1 mL Destillate + 1 mL
KMnO4 (aq) = dark brown
and precipitate
1 mL CH3COOH(aq)
+ 1 mL KMnO4 (aq) =
Purple

Before :
CH3COONa (aq)=
colorless
FeCl3 5% = Yellow
After :
CH3COONa (aq) + FeCl3
5% = Red
After Heated
CH3COONa (aq) + FeCl3
5% = formed precipitate
and the solution is
colorless after filtered
Residue = brownish Red
Filtrate = Colorless

3CH3COONa

Reaction of acetic acid

(aq) +

and

3FeCl3(aq)

brown

3CH3COO- +

in reaction that occur is

Fe3+ +

oxidation

3NaCl(s)
NaCl(s) +
K4Fe(CN)6 (aq)

[Na4Fe(CN)6]
+ 4KCl (s)

cause the result of filter

FeCl3

precipitate and

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Filtrate + K4Fe(CN)6 =
green soft
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reaction.

It

is ferro ion. It can detect


because when the filter
react with K4Fe(CN)6 the
color is soft green, its
different with FeCl3 5%
that

have

yellow.

produce

color

is

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FeCl3 5% comparative =
yellow

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Esterification Reaction

- CH3COOH(aq) +

Before =
CH3COOH glacial =
colorless
Ethanol 96% =
colorless
H2SO4 concetrated =
colorless

C2H5OH(aq)
CH3COOC2H5 +
H2O(l)
C2H5OH(aq) +
H2SO4 (aq)

After
Test tube 1
CH3COOH glacial +
Ethanol 96%+ H2SO4
concetrated = colorless
After Heated
CH3COOH glacial +
Ethanol 96%+ H2SO4
concetrated = colorless
and produce odor like
as rubber

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Test Tube 2
Ethanol 96%+ H2SO4
concetrated = colorless
After heated Ethanol
96%+ H2SO4
concetrated = colorless
And produce odor that
sting

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If glacial acetic acid


react with ethanol occur
esterification reactionit
known by the odor
Ethanol reacting with
H2SO4 not occur
esterification reaction

H. Analysis
1. Preparation of formic acids and reactions happen in formic acids
On the frist experiment aims for Preparation of formic acids and reactions
happen in formic acids . First, Count weight of 5 gram oxalic acid (H2C2O4) white
crystalline and count weight 5 gram glycerol ( colorless and viscous solution) .
Next, pour boiling stone in the destillation flask functioning for flatten heat to all
parts of the solution. Then entered 5 gram oxalic acid and 5 gram gliserol in the
destillation flask , so that mix become colorless viscous solution and there insoluble
crystall oxalic acid. Add glycerol have function ie as catalyst which accelarate
preparation of formiac acid. And then heated. The Solution change color become
soft yelow and form gas. Gas is formed ran in the lime water for checking
destillation process running with appropiate after while lime water change become
turbid solution . it shows that gas formed is gas CO 2 because gas carbon dioxyde
reacting with lime water can be form CaCO3 , so that lime water become turbid. The
reaction :
CO2 (g) + Ca(OH)2(aq) CaCO3(s) + H2O(l)
After lime water become turbid solution , heating is . and then added 2,5
gram oxalic acid (H2C2O4) into destillation flask . Addition of oxalic acid is made to
add reactants which aims to shift the reaction to the right (product). Due to obtain
yield much, equilibrium should be shifted towards the product. by using one of the
substances in excess perekasi cheap, in this experiment was added oxalic acid. Then
reheated to get distilatnya (formic acid). After some time, formed a colorless
distillate .
Reaction :
H2C2O4 (s)

HO C 4 H 8 OH

HCOOH (aq) + CO2 (g)

After it Destillation will stopped After the distillation is stopped, a colorless


distillate is measured in volume, so that it can be seen distillate gained as much as 1
mL. To determine whether the distillate is formic acid, then tested by means of
identification with KMnO4 1 mL of distillate put into a test tube and then added 1 mL
of solution KMnO4 is purple, so that the mixture of distillate and KMnO 4 to a

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solution become brown and there are black precipitate. This is because the addition
of KMnO4 act as an oxidant.
Then make the compare solution by entering a 1 mL CH 3COOH into a test
tube and then added 1 mL of solution KMnO 4 also the color purple, so the mixture
becomes thick purple solution. From the experimental results, after Destillate drops
of KMnO4 , distillate becomes brown due to the oxidation of formic acid susceptible
when reacted with KMnO4 to produce CO2, then this is the function of KMnO4
which acts as an oxidant. Permanganate that is reduced to Mn 2+ is what causes the
appearance of a brown color.
The Reaction Is :
3HCOOH(aq) + 2KMnO4(aq) 3CO2(g) + MnO2(s) + 2KOH(aq) +
2H2O(l)
While the reaction tube 2 purple solution was concentrated. It showed no
redox reaction occurs, which is characterized by the dont formation of MnO 2
precipitate in the form of brown. From the equation occur, KMnO 4 oxidizes formic
acid. This is due to acetic acid binds with a methyl group on the carboxyl group
while formic acid is only bind H+ so that when reacted with KMnO4 formic acid will
be more easily oxidized to form MnO 2 than acetic acid, then the acetic acid was not
contained precipitate and color of the solution remains purple as KMnO 4. The
reaction equation:
3CH3COOH + 8 KMnO4
2. Acetic Acid Reaction
The second experiment is acetic acid reaction. The purpose of the second
experiment is to understanding the principle of carboxylic reaction (oxidation). In
this experiment 5 mL of sodium acetate (10%) that colorless react with 3 mL of
FeCl3 that yellow, adding FeCl3 is to produce ferric precipitate. But after adding
FeCl3 is not formed precipitate just red color solution. From this reaction produce
red solution. It is caused the solution contain ferric acetate. This is appropriate with
this equation bellow:
3CH3COONa+FeCl3 (CH3COO)3Fe+3NaCl
(Raj, 2009: 28)
After that the solution heating and the solution formed brown precipitate. It cause
after heated the solution (CH3COO)3Fe changed be CH3COOFe(OH)2. This is
appropriate with this equation bellow:
(CH3COO)3Fe+2HOH

Heated

2CH3COOH+CH3COOFe(OH)2
(Basic Ferric acetate)

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(West, 1920: 126)


After get the precipitate, filtered the solution. It is to separate the filter and the
residue. The residue is the precipitate. And the filtrate will analyze, are the filter
contain ferric ion or not. After the filter react with K4Fe(CN)6 1 M the color of
solution changed be soft green. This result compared with the color of FeCl 3. The
color of FeCl3 is yellow but the filter after adding K4Fe(CN)6 is soft green. It means
that the filter is not contain ferric ion but the filter is contain ferro ion. It caused the
oxidation reaction, the reaction can write bellow:
Fe2+ + [Fe(CN)6]3- Fe3+ + [Fe(CN)6]4+2

+3
Oxidation

So from this experiment can conclude that reaction of acetic acid and FeCl 3 produce
brown precipitate and in reaction that occur is oxidation reaction. It cause the result
of filter is ferro ion.

3. Esterificarion Reaction
In this experiment aims to understand the principle - the principle of a
carboxylic acid reaction is an esterification reaction. First, set up two test tubes. In
the first test tube, put 2 mL of glacial CH 3COOH in the form of a colorless solution.
Then added 2 mL of 96% ethanol in the form of a colorless solution, and then added
8 mL of concentrated H2SO4 in the form of a colorless solution. So that the mixture
became a colorless. The function of add concentrated H 2SO4 is a catalyst, which is
to reduce the activation energy of the reaction so as to accelerate the formation of
ester (esterification). Then the reaction tube is sealed using aluminum foil. It is
intended that the compounds do not evaporate when heated
In the second test tube, inserted 2 mL of ethanol 96% in the form of a
colorless solution. Then added 4 mL of concentrated H2SO4 in the form of a
colorless solution. So that the mixture became a colorless solution. The function of
add concentrated H2SO4 is a catalyst. Then the reaction tube is sealed using
aluminum foil. It is intended that the compounds do not evaporate when heated.
After that the two tubes are heated to cause odor. Heating function is to accelerate
the esterification reaction or accelerate the formation of esters. After a while, inhaled
the smell, the tube 1 produces fragrant smell like Rubber. Reaction :
CH3COOH(aq) + C2H5OH(aq)

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H2SO4

20

CH3COOC2H5 (aq) + H2O (l)

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The reaction is an esterification reaction to produce ethyl acetate fragrance


like a rubber. The smell is distinctive odor of the ester compound.
While on the tube 2 smelly. This indicates that the esterification reaction
does not occur on the tube 2. The equation Reaction is:
C2H5OH (aq) + H2SO4 (aq)
From the reaction does not produce esters for this reaction is a substitution
reaction not esterification reaction.

I.

Coclusion
From explanation above can conclude:
1. Formic acid can produce from decarboxylation of H2C2O4 with use catalyst
glycerol and the other product is CO2 and the function of KMnO4 is as oxidator.
2. Reaction of acetic acid and FeCl3 produce brown precipitate and in reaction
that occur is oxidation reaction. It cause the result of filter is ferro ion. It can
detect because when the filter react with K4Fe(CN)6 the color is soft green, its
different with FeCl3 5% that have color is yellow.
3. If glacial acetic acid react with ethanol and sulfuric acid occur esterification
reaction. It can known by the odor. The odor is like rubber. But ethanol react
with sulfuric acid is not occur esterification reaction and the odor is sting.

J.

Referencess

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Cason, James. 1956. Essential Principle of organic Chemistry. USA: Prentice hall,
Inc
Fessenden, Ralp J., Fessenden, Joans.1982.Organic Chemistry 3rd Edistion, 2nd
Volume. Jakarta: Erlangga
Raj, Gurdeep. 2009. Advanced Practical Inorganic Chemistry. Delhi: Goal
Publishing House
Sutcliffe, Arthur. 1930. Practical Chemistry for Advanced Students. London: John
Murray
Tim Dosen Kimia Organik. 2016. Penuntun Praktikum Kimia Organik I. Surabaya:
Jurusan Kimia FMIPA UNESA
West, Augustus. P. 1920. Experimental Organic Chemistry. New York: World Book
Company

K. Attachment
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1. Task And Question


1. Write the reaction that occur at the experiment ?
2. Explain the specialty of formic acid than carbixylic acid ?
3. What the function of H2SO4 at the reaction of ethanol and asetic
acid ?
4. Reaction between ethanol and sulfuric acid can produce the
other result besides ethyl sulphate, based on the temperature
reaction. Explain the statement ?

Answer
1. Reactions
a) Preparation and Reaction of Formic Acid

H2C2O4(aq) 150 C
HCOOH (aq) + CO2 (g)
Oxalic acid
formic acid
(CH2)CH(OH)3
CO2(g) + Ca(OH)2 (aq) CaCO3(s) + H2O(l)
Hydrated lime
2 HCOOH (aq) + 2KMnO4(aq) 3CO2(g) + MnO2(s) +

2KOH + 2H2O(l)
CH3COOH(l) + KMnO4(aq)

b) Asetic Acid reaction

3CH3COONa (aq) + 3FeCl3(aq) 3CH3COO- + Fe3+ +

3NaCl(s)
NaCl(s) + K4Fe(CN)6 (aq) [Na4Fe(CN)6] + 4KCl (s)

c) Esterification Reaction

CH3COOH(aq) + C2H5OH(aq)
H2SO4
+ H2O(l)
C2H5OH(aq) + H2SO4 (aq)

CH3COOC2H5

2. Specialty of formic acid than carboxylic acid are :


Formic acid Specialty compared with other carboxylic acids:
Formic acid is a carboxylic acid having one carbon may be
prepared by reaction of decarboxylation with oxalic acid,
can undergo oxidation reactions when reacted with KMnO 4,
undergo esterification reaction when reacted with alcohol

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and produced ester (fragrance), but the carboxylic acid

which others formed from different functional groups.


Physical properties of formic acid is a colorless liquid,
pungent and completely soluble in water. While the
chemical properties of the formic acid is the most powerful
acids from carboxylic acids other and have the acid group
and an aldehyde. Formic acid can be made from the

reaction of oxalic acid decarboxylation (H2C2O4).


As the carboxylic acid: Can form salts, can form esters and
acid chlorides can form hydrochloric acid formed but
unstable

3. The function of sulfuric acid at the reaction of ethanol and


acetic acid is a catalyst.
The function of H2SO4 in reaction between ethanol and
acetic acid is as a catalyst for lowering the activation energy
so as to accelerate the rate of esterification reaction, thus
forming ester and will eventually form again as H2SO4.
Equations:
CH3COOH(aq) + C2H5OH(aq) + H2SO4(aq) CH3COOC2H5(aq) + H2O(l) + H2SO4(aq)
The mechanism of the reaction:
Stage 1 :

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Stage 2 :

Stage 3 :

Stage 4 :

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Stage 5 :

4. The reaction between ethanol and sulfuric acid can produce


other products besides ethyl sulfate, depending on the
reaction temperature. Explain that statement!
Answer:
If ethanol is heated with concentrated sulfuric acid are
dehydrated. At a temperature of 140 to form ether.
H 2 SO 4(140 )
2C2H2OH
C2H5OC2H5 + H2O

If ethanol is heated with concentrated sulfuric acid at a


temperature of 180 will produce alkenes
H 2 SO 4(180 )
C2H2OH
CH2=CH2 + H2O

Ethanol and concentrated sulfuric acid occurs a series of


reactions.

In

general,

the

primary

alcohol

at

low

temperature will produce sulphate ester, at medium


temperature

to

produce

esters,

whereas

at

high

temperatures will produce alcohol. Ethanol and sulfuric


acid can produce other products besides ethyl sulfate,
depending on the reaction temperature. This could occur
because the temperature can affect the rate of reaction
and may also affect the results of the reaction so ethanol
and sulfuric acid can produce other products besides
ethyl sulfate.
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